HCID 68738138, compound → HCID 68737323, compound

HRID 529162Notes

Reaction equation

HRID 529162 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[Br:22])[NH:15][C:14]2=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[Br:22])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68738138HCID 68738138, compound

Product 1

HCID 68737323HCID 68737323, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1′-benzyl-4-bromospiro[indoline-3,4′-piperidin]-2-one (12.0 g, 32.3 mmol) in THF (300 mL) was carefully treated with the addition of BH3-THF complex (97 mL, 97 mmol). The reaction was then heated at 80° C. for 24 hours. The reaction mixture was quenched by the addition of 1N HCl. The aqueous layer was extracted with EtOAc (3×100 mL). The aqueous layer was basified to a pH of 12 with NaOH pellets and extracted with EtOAc (3×200 mL). The organic layers were dried with MgSO4 and concentrated under reduced pressure to give 1′-benzyl-4-bromospiro[indoline-3,4′-piperidine] (7.3 g, 63%) as an oil. LCMS (APCI+) m/z 357/359 [M+H]+; Rt=3.07 min.

Workup

  1. customThe reaction mixture was quenched by the addition of 1N HCl
  2. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. dry with materialThe organic layers were dried with MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea3b2c3981124e96b5a87ab008ea79e9
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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